Managing Expectations
Or, How I Learned to Stop Worrying About What You Think and Love the Process
They say writing is rewriting.
That is the truth I have been living deeply in for the past couple of months. I’m just getting started. Hey Google, what’s that word for when you’re afraid of sounding generic so you keep your thesaurus tab open, only to find that the generic word you were going to use doesn’t mean what you think it means?
Oh, and by the way… I will not be proofreading or editing these posts. There is no rewriting here. And I fired Grammarly. Managing expectations.
I have been writing for screenplay format for the better part of the past six years and have trained a lot of the basics of traditional writing out of me. It has been exceedingly more challenging than I thought to go back to narrative prose. Will I write in first person or third person? Present tense or past tense? How do I go from a dialogue-dependent medium to one where dialogue is used sparingly? How do I choose which one of my four metaphors to use? I love them all. A love like a car alarm in a quiet neighborhood… loud, uninvited, and absolutely certain of its own importance. A love like an airport Cinnabon… you knew it was a bad idea and you wanted it anyway and the wanting made no logical sense given everything you knew about yourself. A love like…
See?
So how did I get here? Earlier this year I heard about the Paramount Writer’s Mentoring Program. A Screenwriting fellowship that accepts applications from writers, and when selected, puts them in a sort of writer’s room bootcamp. It’s an incredible opportunity, one that I had no grand delusions about being selected for. But it was a goal, a marker. And I was attracted to that. So I set out to enter. The prerequisites were that you must enter a spec script of an existing show, plus an original television pilot script, of which I already had a couple. So I thought… the task in front of me was to write a spec of a show I love, and send in that plus a script I already had in the can. And I’m golden.
For my spec script I chose Shrinking. The razor sharp edge of comedy and drama that the show walks felt very aligned with my style, and what I believed I could tap in to. Within a few weeks I had my first draft, and after a few more weeks I had smarter writers look at it for me, who helped me get it that much better. I was pretty happy, I must admit.
The due date for everything was Friday, May 1, 2026.
On Sunday, April 26, 2026 I decided to re-read the rules on the Paramount website once more. Just to make sure I had everything I needed for submitting. And? Well, As I read my heart sank. The two writing samples… APPARENTLY… had to be in the same genre. The original pilot script I had planned on sending in was NOT… by any means… within a mile of the genre of Shrinking. So I sat there. At 5:00 PM on the Sunday before the Friday, this was all due. Do I just throw in the towel? Chalk it up to a good experience? I mean, I did end up with a good spec script after all… Or do I try and pull off an original TV pilot script in the next 5 days?
You probably know where this is going…
I have a habit of biting off more than I can chew. At least I am consistent. I went for it. I opened the notes app on my phone and found the entry where I had entered in ideas… a couple years ago. I found one in particular that stuck with me. I went for a walk around the block and banged the idea out in my head… seeing if it had legs. And really, it wasn’t even a complete idea in the notes entry. It was simply a title. Two words: The Understudy. But I remembered what I meant when I typed it in years ago.
An actor who is perpetually cast as the understudy in his community theatre productions has to go on one night, and it changes everything.
That was all I had.
So I am on this walk. Sussing the idea out. What else is there to it? So I have the external event. What does the pilot episode build up to? A big moment, like a song? What song? What is happening emotionally? And what is the play or show that everything revolves around? Obviously, it has to be metaphorical for the character. Obviously. So what could it be? What would work?
I lost my mom in a car accident in January of 2025. Everything that day happened so quickly. The phone call from the EMT around 1:00 PM. Waiting at the hospital through the afternoon as the prognosis got worse and worse. Until finally, in the early evening, there was nothing left to do but to let her go.
Until you have lost a parent, there is no way to describe it properly. In a way that you will truly understand. That’s okay. I wouldn’t want anyone to understand. A sudden feeling of breaking off, and floating in the endlessness without an oar that up until that moment you believed was as essential as the air you breathed. Because it was. You just never thought about it. And now here you are having to figure out your way without it. So it’s fine if you don’t understand. But maybe, this part you will…
While on my walk, while trying to piece together the idea for this show, and what the connective tissue would be emotionally, and what the driving engine would be externally, aka the show, the music. My mom showed up. I genuinely felt her arms on my shoulders as I walked. It was comforting and surreal and all the things.
One of her favorite musicals was Man of La Mancha. And one of her favorite songs was “The Impossible Dream.” If you know the show, you know it’s about a knight who has these hallucinations and thinks windmills are giants. But there’s more to it than that. It’s about a man who, in spite of his place in the world, dares to dream. Once all this was flowing through my head… a gift of realization from my mom. I saw it all. The story, the characters, all of it.
So during the next three days, I wrote the first draft of the pilot episode for The Understudy. I got up early and went for an hour-long walk, dictating into my voice memos. On my lunch breaks and into the night, I transferred these to text and went from there. So on and so forth. Until that first vomit draft was complete on Wednesday, April 29.
Then came the rewriting. Remember that?
On Friday, May 1st, at 5:00 PM, I turned everything in. It wasn’t perfect. But it was done in time.
And I had this world and these characters. And these themes. And this personal connection. A deep, deeply personal artery system buried inside something I wrote. And this is something I had never experienced before.
Long story (long post?) short. What began as an exercise to write a 30-minute comedy TV pilot has now morphed into writing a novella. One that explores the themes of the pilot, stretched out across a longer narrative arc, and with more introspection than I had planned when it was just a script (which are notoriously sparse and basic).
As I attempt this project of writing, I will check in here periodically and share a bit about the process. One of my goals is to encourage other writers to go and do the thing eating at them, if there is a thing they feel they need to do. Another goal is to manage expectations. This is my first time writing a novella, let alone anything like this. Or sharing it. Or publishing it. So go easy on me. Don’t expect perfection.
But how many of our favorite authors came out of the gate with a perfect novel anyway?
Be on the right side of history. Go easy on me.
Se you soon,
Calvin
